I did use Esri World Imagery, though. It's more up to date here than Bing, albeit a tad blurry

I picked an old source from dropdown box in JOSM. I did not, in fact, use "USGSHydroCached" national hydrography dataset

I added the name "State Highway DD" to reflect that locals refer to this road as though it were part of Route DD, however MoDOT makes it quite clear that they don't consider this part of the route.

It should not be added to the route relation for Missouri Route DD.